HCID 67377818, compound → HCID 10352977, compound

HRID 1182722Notes

Reaction equation

HRID 1182722 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=3[CH2:15][O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[F:22][C:19]1[CH:20]=[CH:21][C:16]2[CH2:15][O:14][C:11]3([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:17]=2[CH:18]=1

Participants

4

Reactant 1

HCID 67377818HCID 67377818, compound

Product 1

HCID 10352977HCID 10352977, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1′-benzyl-6-fluoro-3H-spiro[2-benzofuran-1,4′-piperidine] (1 g, 3.4 mmol) in ethanol (10 ml) was added Pd/C 10% (100 mg, 0.09 mmol). The mixture was refluxed under an hydrogen atmosphere for 8 hours then cooled to room temperature and purged with argon. The catalyst was filtered and the filtrate was concentrated in vacuo to yield 0.67 g (96%) 6-fluoro-3H-spiro[2-benzofuran-1,4′-piperidine] as a white solid. MS m/e: 208 (M+H+).

Workup

  1. temperatureThe mixture was refluxed under an hydrogen atmosphere for 8 hours
  2. custompurged with argon
  3. filtrationThe catalyst was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-197a5d36bb8f4a30a15484193c912f40
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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